Hexamethyldisilazane → HCID 59164836, compound

HRID 418368Notes

Reaction equation

HRID 418368 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[C@@H:15]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:18][CH:17]=2)[CH2:14][CH2:13][C@H:9]1[C:10](O)=[O:11])=[O:7])([CH3:4])[CH3:3].CC[N:32](C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C[Si](C)(C)N[Si](C)(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C.O>[NH2:32][C:10]([C@@H:9]1[CH2:13][CH2:14][C@H:15]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:18][CH:17]=2)[N:8]1[C:6]([O:5][C:2]([CH3:4])([CH3:3])[CH3:1])=[O:7])=[O:11]

Participants

8

Reactant 5

HCID 13838HexamethyldisilazaneHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59164823HCID 59164823, compound

Product 1

HCID 59164836HCID 59164836, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (5R)-1-{[(1,1-dimethylethyl)oxy]carbonyl}-5-{4-[(phenylmethyl)oxy]phenyl}-L-proline (1.44 g, 3.62 mmol) in dry DMF (20 ml) were added DIPEA (1.26 ml, 7.24 mmol), then TBTU (1.23 g, 3.98 mmol) and after 20 minutes, 1,1,1,3,3,3-hexamethyldisilazane (1.15 ml, 5.43 mmol). The reaction mixture was stirred at room temperature for 2 h, then it was treated with aqueous 5% NaHCO3 solution (30 ml) and stirred for further 30 minutes. The resulting mixture was diluted with water and extracted with ethyl acetate. The organic phase was then washed twice with brine/ice, dried over Na2 SO4 and evaporated to give a colourless oil. This crude material was purified by chromatography on silica gel eluting with cyclohexane/ethyl acetate (7:3 to 5:5) to afford the title compound (1.25 g, 87%); Rt (HPLC): 5.51 min; Rf (cyclohexane:ethyl acetate=1:1): 0.29. MS: (ES/+) m/z: 419 [M+Na+]; C23H28N2O4 requires 396.

Workup

  1. stirringstirred for further 30 minutes
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was then washed twice with brine/ice
  4. customdried over Na2 SO4
  5. customevaporated
  6. customto give a colourless oil
  7. customThis crude material was purified by chromatography on silica gel eluting with cyclohexane/ethyl acetate (7:3 to 5:5)

Sources & evidence

ORD record
ord-955bbf4f1f6d476ea15b5dfb16698b5c
Source dataset
uspto-grants-2012_01
Patent number
US08093268B2

Reaction notes

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